Month: April 2023

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Three Lessons For Creating Unforgettable Experiences

games, playing, child

As those close to me know, over the past few weeks, I’ve been knee-deep in some new projects. Projects I haven’t been this excited to produce in a long while. One of which is around experiences.

At the same time, as friends and long-time readers of this humble blog know, I am no stranger to the world of social experiments and experiences. I still don’t have a great catch-all term for it. They’re not just another set of “events.” Events just remind me of the same conference, fireside chat, or happy hour playbook. But I try to take my events a step further. So, naturally, given my fascination around building experiences, I walk hand-in-hand with both psychological research and game design. The former of which I share a bit more in previous blogposts than the latter.

So, I’m going to dedicate this essay to three of the lessons I picked up in the latter.

  1. Create experiences that optimize for people who know no one else there.
  2. Don’t confuse complexity with depth.
  3. A great event is great not due to the event itself, but because of the story one gets to tell again and again.

1. Create experiences that optimize for people who know no one else there.

I had always had this somewhere in the back of my head. To design experiences where no one was ever left out. But when I caught up with a friend recently in New York, he codified it into what it is today. As someone who runs a design studio that builds immersive experiences in New York, he spends most of his time building experiences for strangers. And while friends may visit his exhibits together, the vast majority of his attendees do not know anyone else.

Take, for example, happy hours. Most happy hours aren’t designed for the person who knows no one. Usually the event itself is fairly laissez-faire. Most of which, the hosts don’t actively try to connect attendees. And so if you show up at a happy hour and the host is too busy to intro you to anyone, unless you’re an outgoing person, you’re likely standing near the edges, hoping to jump into a conversation if any group will let you. This often leads to events where people leave early and form cliques. It also optimizes for early birds, rather than the fashionably late.

Tactically, it’s creating excuses for people to jump in conversation. While not a problem for outgoing individuals, I need to empower everyone, including shy introverts, with tools to start conversations, where I and/or the experience shoulder the initial responsibility and blame to start conversations. That could be with customized fortune cookies where one is supposed to read their fortune to someone else. Or empowering people with a mission or an ask greater than themselves. For instance, to over-simplify it a bit, “I’m trying to put together a small group of everyone who’s wearing glasses tonight. Do you mind helping me find out all the names of the guests who are wearing glasses?” Or “I’m trying to resolve a debate with my co-host. Pineapples or no pineapples on pizza. I’m all for pineapples, but she isn’t. Can you help me find more allies?”

2. Don’t confuse complexity with depth.

This is unfortunately a fallacy I often find myself spiraling down the longer I’m given to ponder. And I lose myself in intellectual complexity.

Many years ago when a couple friend and I first decided to host an escape room in a mansion over three days and two nights, the greatest question we had was: How do we create an immersive experience over multiple days? And retain that level of immersion throughout? I thought, hell, what if we created a brand new language for the event. One that all guests would have to learn and practice throughout the event. We’d ease them in slowly, but the biggest puzzle could only be solved through adequate mastery in this new language. This easily gave me the greatest injection of dopamine when planning for the event. And I went deep, talking with linguistic professors, studying how Tolkien created Quenya, and how Cameron and Paul Frommer created the Na’vi language.

It was truly interesting to me and to many of my friends. But unfortunately, through user testing, to most others, while interesting to hear its backstory, was not fun to practice. I had ended up developing it to a level to where it departed from its English roots to resembling language of Scandinavian origin. Because of its complexity and how there were more guests who were English speakers than speakers of this new language, immersion broke almost instantaneously.

The great Mark Rosewater once defined interesting as intellectual stimulation and fun as emotional stimulation. While they’re not mutually exclusive, it’s important to not confuse the two.

There’s a great Maya Angelou line that I, like many others, like to reference. “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.” And it is no less true for gamified designs. Emotional satisfaction often runs deeper and longer than intellectual satisfaction. The former has a greater chance of becoming a “core memory,” to borrow from the brilliant minds behind Pixar’s Inside Out, than the latter.

I was lucky to learn this lesson from one of the greatest designers of card games alive today. It was on a call earlier this year, where I was telling him about all the awesome bells and whistles I was planning on implementing for an upcoming experience. And I asked what he thought. To which, he responded: “Kill all complexity. Complexity is not a substitute for depth. Rely on your audience for depth. The more borders, the harder it is enjoy. Too few, it’s chaotic. Find the absolute minimum number of borders.”

The goal of creating systems is to create opportunities for serendipity. To create opportunities where people can dive deep. Not to force people to take the plunge when they may not be ready.

His advice just happens to rhyme with a quote I’ve always kept somewhere in the back of my mind, but now sits on the wall above my PC.

“Your ability to solve problems with magic in a satisfying way is directly proportional to how well the reader understands said magic.” — Sanderson’s First Law of Magic

3. A great event is great not due to the event itself, but because of the story one gets to tell again and again.

Under the ambiance of MarieBelle, which I still so fondly remember the moment my friend told me this, she said, “A great event is great not due to the event itself, but because of the story one gets to tell again and again.” It’s the truest definition of surprising and delighting. She was someone who used to work on the Dreamweavers team at Eleven Madison Park when Will Guidara was still there. As such the above lesson was a page out of Will Guidara‘s book Unreasonable Hospitality, whose best known for how intentionally he took front of the house hospitality at 11 Madison Park, one of the greatest restaurants in the world. 4 stars on New York Times, and 3 Michelin stars. He also happened to be the person who conceived the Dreamweavers team there. Just to give you an idea of how seriously they take their roles…

First off, the core of the event itself — the meat, the protein — has to be great. If it’s a tofu burger, it better be a damn well-marinated fat slice of egg tofu, double-fried to perfection. To Malcolm Gladwell, that’s the meal.

And only once you have it all, what’s the cherry on top? What’s the candy? Why would people want to talk about it? For events, that’s:

  • Delivering surprises — gifts and/or experiences they do not expect
  • Transferrable pieces of knowledge — insights, frameworks, or trivia knowledge that are useful even after the event
  • Meeting great people WITH great stories — “Did you know that [so-and-so] did X?” And for this to happen not just opportunistically but at scale, finding ways to help people share stories of vulnerability or of adventures that have yet to grace any public media is key. The easiest way is through questions. The slightly harder way is through a set of triggers where it makes sharing such a story natural.

In closing

I am, as always, a work-in-progress. And with the events I’ll continue to host this year, I’m going to learn more. And in time, be able to share more of my lessons, trials, and tribulations in this journey. In hopes, this will aid or inspire you on your path.

Photo by Holly Landkammer on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

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How to Retain Talent When You Don’t Have the Cash

lightning in a bottle, spark, hold, light, jar

Earlier this week, I grabbed coffee with a founder. Let’s call him “Elijah.” He recently lost a key exec he’d been working with for two years to their incumbent competitor. The competitor’s offer happened to be too good to turn down. Triple the exec’s salary. As that exec had a family to feed and children’s education that didn’t come cheap, he made the hard decision to leave. Needless to say, Elijah was devastated. And he asked,

“David, what should I have done?”

I initially thought it was rhetorical. It seemed that way. But he paused, looked at me, and waited.

So I responded.

My response

I’ll preface by saying that the advice I shared with him was a collection of insights I learned from mentors over the years — some a lot more recently than others. I don’t hold all the keys to the castle. And every situation is, well, situational. So the last thing I wanted was for the founder to take my advice as the word of god (nor anyone reading this blogpost now). Merely a tool in the toolkit. At times, useful. Other times, just something that acts as décor in the shed.

“Elijah, it’s probably too late for that exec… for now. He’s made his decision and walked. That said, I think there are two things to be aware of here:

  1. The fact you didn’t know about this until it happened, and
  2. The decision itself.”

Pre-empting the ultimatum

For the former, here’s how I think about pre-empting your team’s career inflections.

  1. In their first week, have everyone put together their personal manifesto. What is their 6 month goal? 1 year? 5 years? 10 years? Lifetime goal? What motivates them? How do they like to give and receive feedback? Of course, it’s helpful to share your own first, so they have a reference point. Don’t expect anything you’re not willing to share first. So, naturally, this requires a level of transparency, and more importantly, vulnerability.
  2. Then within the first two weeks, you and their direct manager should review their manifesto with them for at least 30 minutes live. Really get to know them. Taking a page out of Steven Rosenblatt’s book, what drives them? What haven’t they achieved that they want to achieve? How do they do their best work? When do they feel the most motivated? Why did they want to work here? Why are they excited to do so? How does working at your company fit in their broader goal?
  3. Then every quarter, allow every team member one day of mindfulness away from their work to revisit their manifesto. I usually recommend a Friday. What’s changed? What’s stayed the same? Does their current role still fit in their broader goal? If not, why not?
  4. The week after, take time to sync again and be incredibly candid.

Of course, the above is easier to do if you have a company of less than 50. At some point, when your company scales past that, it’s at least helpful to do it with your direct reports and their direct reports.

Helping with the decision

For the latter, you can’t stop a river. Even if you build a dam, the flow will always find a way around. You can’t change what motivates someone else. But you can help them channel it. The best thing you can do is equip that person with the tools to make a decision they will not regret, and wish them the best.

I like to sit people down and first help them figure out why they’re considering a new role. People often conflate the three traits of a job — compensation, scope, and title — together when making a career move. But in truth, they’re similar, but all a bit different. And I want people to know that just because they’re getting paid more doesn’t necessarily mean an increase in responsibility. Just because they’re getting a new title doesn’t mean that they’ll get more money. Then I have them stack rank the three traits. From most to least important.

If they still rank compensation first, that’s fine. Maybe they’re saving to buy a new house or to pay for their child’s higher education. And there’s nothing you nor I can do there. But if it’s one of the other two that come out on top, there’s room to create a new position or set of responsibilities where the individual feels empowered. And if it’s not at your company, they’ll be equipped to think through it at their next company. If they don’t have one lined up yet, help them through your network find one that’ll fit the criteria.

The wonderful irony

The funny thing about helping people achieve their dreams — sometimes that’s actively helping them leave your company — is that the karma usually comes back in one way or another. In this case, and I’ve seen it and experienced it before, even if you lose this person at this time and place, they’ll remember the help you gave them. To which, one day, when they have an all-star friend looking for their next opportunity, they will think of you.

There’s a saying I love. ‘The best compliment an investor can get is to get deal flow from someone they passed on.’ And here, the best compliment you can get is to get talent from someone who left your team.

In closing

Shake Shack’s Danny Meyer recently said something that echoes this notion. While he uses the word “volunteering,” he defines “volunteering” as:

“I basically, to this day, treat all of our employees as if they are volunteers, which not in the real sense. You’re going to get paid. But if you’re working for me, it means you’re probably good enough to have gotten another 25 job offers at least. And so, as far as I’m concerned, you’re volunteering to share your gifts with us.”

He goes on to say, “I didn’t have any way to motivate them with money. I couldn’t give them a raise, couldn’t dock them their pay. So I learned such a crucial lesson, which is that, if someone’s volunteering, the only way to motivate them is to have a higher purpose.”

Of course, there’s more than one way to make a team member feel like they are valued and that they value their work here. Another way is to give your prospective team member a “love bomb”, as Pulley’s Yin Wu calls it.

Now I’m not saying that if Elijah did all the above, he’s guaranteed to retain the exec. Who knows? He might have. Might not. For a man with a family and financial needs, it’s a hard ask. But at the minimum, this career move wouldn’t have blind-sided him. And better, he could’ve supported that exec in making that career move.

Just like with your product, your goal with your team is also to catch lightning in a bottle. How do you attract the best talent to work with you? And then, once you are able to, how do you keep them?

With the latter, a big part of it is showing you care.

Photo by Diego PH on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

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What It Means to be Antifragile

boxing, antifragile, resilient

The thing is this is the first real recession I’m working in. I entered the workforce something in the midst of one of the longest bull markets in modern history. So, naturally, I had a lot of questions. One of which I asked one of my mentors in VC who’s been through a few cycles late last year. “Are there any leading indicators that foretell when we’re going to get out of a recession? Or when we truly hit rock bottom in a recession?”

And he said something that made complete sense. “When the frequency of mass layoffs, especially from some of America’s largest employers, slows to a halt.”

Since then, every month or so, I check in the number of WARN notices that come in which require companies doing a mass layoff to publicly report a layoff 60 days in advance. For instance, you can find California’s here.

As Chamath Palihapitiya puts it in his 2022 annual letter, “while we believe that most of the multiple contractions in these markets have largely worked their way through the system, we suspect there is still some more room to fall — particularly if the U.S. enters a recession in the coming year.” Since it seems layoff season is yet to pass, it seems wise to buckle in for the longer run.

While friends have asked me when the recession will end, I responded with a simple “I don’t know.” No one does. And while many may make conjectures on the timing, the one thing we can use this free fall for is to build a heat shield.

I really like this one line in Chris Neumann‘s recent blogpost on antifragility. “As great as it sounds for a startup to get stronger when unexpected events occur, I don’t actually think that’s a realistic goal for most companies (it certainly isn’t the case for VC firms). Rather, I think the goal in making antifragile startups should be to minimize the risk and distraction when unexpected events occur, such that the company can continue to make progress while its competitors are panicking and reacting.” One thing’s for sure. The world is host to a plethora of distractions. Something we won’t be in shortage of. With each black swan event, we will only be left with a surplus of attention stealers.

And I’d be presumptuous to say that the best do not get distracted. Rather the best realize when they are and have ways to get back to a focused flow state. Simply put, it’s helpful to play a game of What if? What if this unexpected shock happens? How will I react when my servers get hacked? How do I react when my cash flow is constrained due to an unpredictable event? And in each broad category of What if’s, do you have a way to hedge the risk?

Sometimes, it’s preparing for the unexpected black swan event.

That’s why code is redundant to prevent the fragility of storing it only on one server.

It’s why companies like HackerOne exists.

It’s why you should have your cash in multiple bank accounts, with at least one of them being a big 4. A few top firms, including General Catalyst, Greylock, and Redpoint, have also said, “Keep two core operating accounts, each with 3-6 months of cash. Maintain a third account for ‘excess cash’ to be invested in safe, liquid options to generate slightly more income.” All to protect against the downside risk of losing all your money when you put your eggs in one basket.

But when the black swan does hit, prioritization matters even more. When the pandemic hit and Airbnb was between a rock and a hard place, Brian Chesky described it, “We realized not everything mattered. And it was like if you have to go into a house — your house is burning — and if you could only take half the things in your house, what would you take?”

Chamath went on to write in the same letter. “The most alarming consequence in startup-land has been the divide it has created between the management teams who have ‘found religion’ (i.e. made the tough decisions and managed their businesses smartly) and the rest who are trying their best to avoid reality.” And those tough decisions include, “cutting non-core projects, lowering costs, and vastly reducing G&A while getting to profitability [which] is now mandatory — otherwise you will have to face the consequences.” Those same tough decisions set teams up for success in bad times and bear markets.

In closing

Recently on the Tim Ferriss Show, David Deutsch said, “wealth is not a number. […] It is the set of all transformations that you are capable of bringing about.” Similarly, a company’s revenue is not just another number. It is a product of all the miracles that the company willed into existence. Crossing the chasm. Leaping over hurdles.

To take a line out of Nassim Taleb‘s book, “Crucially, if antifragility is the property of all those natural (and complex) systems that have survived, depriving these systems of volatility, randomness, and stressors will harm them. They will weaken, die, or blow up.” We need black swan events to create miracles. And we need miracles to create stronger, more resilient companies.

Trauma strengthens us. You need to bleed to grow scars. You need to feel pain before you grow calluses. The product of each makes one more resilient to pain and injury in the future.

One might call it antifragility.

Photo by Johann Walter Bantz on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

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DGQ 16: What is a story that you’ve told or have yet to tell where you either fight to hold back tears or fight to hold back giggles?

tears

Whenever I host fireside chats, I always ask three questions before the talk begins, usually a week in advance.

  1. What would make this interview the most memorable one you’ve been a guest for even two years from now?
  2. Are there any topics you don’t want to talk about? Or are sick of talking about?
  3. Are there any questions you have yet to be asked, but wish someone were to ask you?

On top of the above three questions , occasionally, I ask a fourth. Do you have a home run story that has gotten you a standing ovation in the past — privately or publicly?

The goal is simple. Despite hours of research and asking mutuals, sometimes I still can’t find anything that’s humanizing about my guest. And I know for a fact that all humans are imperfect. And that imperfection makes each person relatable. Just like when Neil Gaiman met Neil Armstrong. But recently, I’ve fallen in love with a new way to phrase the fourth question.

What is a story that you’ve told or have yet to tell where you either fight to hold back tears or fight to hold back giggles?

On my flight to New York recently, I watched a movie starring one of my favorite actors in the world, Tom Hanks, which inspired this question. And, subsequently this blogpost. A Man Called Otto. Inspired by Fredrick Backman’s A Man Called Ove. And I’m not ashamed to say, I cried during that movie. While Rotten Tomatoes may not give it the score I think it deserves, it was well-written and well-produced. Through it, I realized that powerful stories are powerful not because of how awesome the protagonist is. But by how relatable their weaknesses are. Their limitations. I’ll give an example… to avoid spoiling the afore-mentioned movie.

Spiderman isn’t awesome because he has mutant powers. He’s awesome because he’s prone to all the emotions and struggles, be it love, bullies at school, a horrible boss, and how he acts out against all of that. Spiderman’s much more relatable than a super billionaire who owns all the gadgets in the world or an alien from another planet. He’s just a kid from Brooklyn. Or Queens, depending on which Spiderman suits your fancy. And as Brandon Sanderson once said, limitations are more interesting than powers. Limitations make us human. And characters who exhibit humanness and still somehow overcome impossible odds are stories that are passed from generation to generation.

That said, storytelling, outside the realm of superpowers, is equally as true. In a world where appearance and social capital goes a long way, trying to be perfect, to look perfect, and to act perfect is a fallacy in the modern era. While we know we’re not perfect, as a society, we continue to strive for perfection.

After watching a lot of movies, and in my free time, watching acting lessons (FYI, would fail as an actor, but still find the craft fascinating.), I’ve learned we don’t cry when watching movies because the characters cry easily. We cry because the character is trying to hold back their tears. And we don’t laugh during a show or a movie because the comedian laughs easily. We laugh even more because they’re trying to hold back their own laughter. The narrators and characters we see are a reflection of who we truly are.

In many ways, if someone cries easily, it relieves the audience of the ability, some artists may call it responsibility, to cry. Someone, the actor or actress or character has diffused the tension already. But if they fight to hold back their tears, holding back the floodgates, we as the audience are more likely to cry in their stead.

Now I say all of this because I find most fireside chats and interviews unrelatable. Now it’s a product of many things. And I genuinely believe a plethora of individuals do have something powerful and insightful to share, but the stage needs to be ready for them. It’s rare for guests to drop some head-turning advice in the first 10 minutes. Which means… it’s up to both the host and the guest to hold the audience’s attention long enough, as well as create enough opportunities for the guest to shine. The above question, in my opinion, does both.

So all in all, going forward, rather than asking for a home run story, I will ask for stories where people are just people. And for stories that mean a tremendous amount to the people telling them. That they have no choice but to let even a little bit of themselves out emotionally.

Photo by shahin khalaji on Unsplash

The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.

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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

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